Fenobam
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Names | |
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IUPAC name
1-(3-chlorophenyl)-3-(3-methyl-5-oxo-4H-imidazol-2-yl)urea
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Identifiers | |
57653-26-6 ![]() |
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ChEMBL | ChEMBL239800 ![]() |
ChemSpider | 142953 ![]() |
1434 | |
Jmol 3D model | Interactive image |
MeSH | fenobam |
PubChem | 162834 |
UNII | 078RCY7I27 ![]() |
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Properties | |
C11H11ClN4O2 | |
Molar mass | 266.684 |
Vapor pressure | {{{value}}} |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references | |
Fenobam is an imidazole derivative developed by McNeil Laboratories in the late 1970s as a novel anxiolytic drug with an at-the-time-unidentified molecular target in the brain. Subsequently, it was determined that fenobam acts as a potent and selective negative allosteric modulator of the metabotropic glutamate receptor subtype mGluR5,[1][2] and it has been used as a lead compound for the development of a range of newer mGluR5 antagonists.[3][4][5][6]
Fenobam has anxiolytic effects comparable to those of benzodiazepine drugs,[1][7][8] but was never commercially marketed for the treatment of anxiety due to dose-limiting side effects such as amnesia and psychotomimetic symptoms.[9][10] Following the discovery of its activity as a potent negative allosteric modulator of mGluR5, fenobam has been re-investigated for many applications, with its profile of combined antidepressant, anxiolytic, analgesic and anti-addictive effects potentially useful given the common co-morbidity of these symptoms.[11][12] It has also shown promising initial results in the treatment of fragile X syndrome.[13] It was developed by a team at McNeil Laboratories in the 1970s.[14]
Chemistry
Fenobam is known to exist in five crystalline forms, all of them exhibiting a tautomeric structure with the proton attached to the five membered ring nitrogen. [15]
References
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- ↑ US Patent 3983135 4-Oxo-2-imidazolidinylidene ureas
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- Pages with reference errors
- Articles without KEGG source
- Articles with changed InChI identifier
- Pages using collapsible list with both background and text-align in titlestyle
- Chemical articles using a fixed chemical formula
- Anxiolytics
- Imidazolines
- Lactams
- Ureas
- Chloroarenes
- Orphan drugs
- MGlu5 receptor antagonists
- Abandoned drugs